While Sandra Bullock is famous for portraying a range of romantic leading-lady roles, she has undoubtedly weathered some brutal storms in her love life off-screen.
Over the weekend, the 59-year-old Oscar winner experienced the devastating loss of her longtime partner, Bryan Randall, following a private battle with ALS. He was 57.
The couple first met back in 2015, after he photographed her son Louis’ birthday, five years after her messy divorce from Jesse James, who admitted to having several affairs during their marriage.
Despite her past heartbreaks, the mother-of-two previously raved that she was ‘so glad the universe had [her] wait’ to raise her family with the right person.
‘I found the love of my life,’ Bullock said of Randall in 2021. ‘We share two beautiful children — three children, his older daughter. It’s the best thing ever.’
Upon reflecting on her relationship with the photographer, the actress confessed that she wasn’t too concerned about getting married and was all about putting their ‘children first.’
‘I don’t need a paper to be a devoted partner, devoted mother,’ she said while appearing on the Red Table Talk. ‘I don’t need to be told to be ever-present in the hardest of times.’
As the world grieves Randall’s death, DailyMail.com revisited Bullock’s whirlwind relationship with him and her entire dating history, including past romances with Ryan Gosling and Matthew McConaughey.
Tragic: While Sandra Bullock is famous for portraying a range of romantic leading-lady roles, she has undoubtedly weathered some brutal storms in her love life off-screen, including the recent death of her partner Bryan Randall (seen above in 2018)
Bryan Randall (2015-2023)
Sandra and Bryan began dating several months after first meeting, and even attended Jennifer Aniston and Justin Theroux’s wedding that same year.
The couple do not have any children together, but Bullock has two adopted children — son Louis, 13, and daughter Laila, 11 — and Bryan has an adult daughter named Skylar from a previous relationship.
The actress was in the process of adopting her second child when things got serious with Bryan.
Sandra met Bryan when she hired him as a photographer to take pictures at her son’s fifth birthday, and described him as a ‘saint’ after she informed him she was adopting a second child when they ‘hadn’t been together that long.’
‘I said, ‘Remember that NDA you signed when you photographed my son?’ I said, ‘You know, that still holds.’ He said ‘Why?’ I said, ‘I’m bringing a child home when I come back from Toronto,” Sandra told Jada Pinkett Smith on her Facebook Watch series.
‘He was so happy, but he was scared. I’m a bulldozer. My life was already on the track and here’s this beautiful human being who doesn’t want anything to do with my life, but the right human being to be there.’
She also described her partner as being ‘very Christian’ and a great example to the children. ‘I don’t always agree with him and he doesn’t always agree with me,’ she said, adding: ‘But if they can take away from that and that is where they feel drawn to, he’s the exact right parent to be in this position.’
On Monday, Randall’s family confirmed his death to People.
‘It is with great sadness that we share that on Aug. 5, Bryan Randall passed away peacefully after a three-year battle with ALS,’ the photographer’s family said in a statement. ‘Bryan chose early to keep his journey with ALS private and those of us who cared for him did our best to honor his request.’
‘We are immensely grateful to the tireless doctors who navigated the landscape of this illness with us and to the astounding nurses who became our roommates, often sacrificing their own families to be with ours,’ the family statement continued.
‘At this time we ask for privacy to grieve and to come to terms with the impossibility of saying goodbye to Bryan.’
Love of her life: Sandra and Bryan began dating several months after first meeting, and even attended Jennifer Aniston and Justin Theroux’s wedding that same year; seen in 2018
Chris Evans (2014)
Back in 2014, rumors surfaced that the Marvel star was heavily ‘pursuing Sandra.’
At the time, a source told Us Weekly that the pair attended a dinner party with friends at Craig’s, and ‘spent the night talking until 12 a.m.’
The insider noted that the hunk, who is 17 years younger than the Ocean’s 8 star, is ‘totally her type.’
When asked about the reports, Bullock mused that the media was ‘a little behind.’
‘We’ve since married and it started breaking apart, so we separated,’ she joked to Entertainment Weekly. ‘We filed for divorce, and I hope everyone can respect our privacy. But we’re going to remain friends and share responsibility of the farm animals we’ve taken on, because you just can’t abandon the animals.’
During their brief romance, they were photographed out dining a handful of times.
But back in 2012, Chris revealed to Details that he had a poster of Bullock on his bedroom wall.
‘She’s been his dream girl for most of his life, so it would be a fairy-tale ending for Chris,’ a source told OK! Magazine in 2014.
Brief romance: Back in 2014, rumors surfaced that Chris Evans was heavily ‘pursuing Sandra’ (Evans seen in 2023)
Jesse James (2003-2010)
Bullock and the Monster Garage host, 54, met after she brought her motorcycle-obsessed godson on a trip to West Coast Choppers’s Long Beach headquarters in 2003.
After James gave her a private tour, the star came home to a call to the father-of-four, who she rejected twice.
Eventually, he managed to woo her with a virtual game of 20 Questions.
After assuming he would just ask her questions about cars and motorcycles, they began a ‘courtship of letters.’
‘It was not something I wanted, needed, or looked for, but because he was a stronger person than I was, spiritually and on a tolerance level, I was lucky enough that he educated me,’ she told Vanity Fair in 2006.
Upon speaking about his preconceived notions about Bullock, James told Nightline in a 2010 that he feared that she would be ‘b**ch and some Hollywood snob and didn’t really give it two thoughts.’
‘I talked to her for a couple minutes and it was like getting hit in the head with a brick. Here’s a woman I had assumptions about and she couldn’t be farther from that,’ James said.
The pair ultimately wed in 2005, in front of 270 of their closest friends and family at a ranch in the San Ynez Valley.
In March 2010, days after she took home an Academy Award for her performance in The Blind Side, several women came forward about their affairs with Jesse.
A month later, Jesse checked himself into a rehab facility in Arizona for sex addiction after apologizing profusely to Bullock, although that wasn’t enough to save the marriage – they divorced the following June.
In 2017, he told DailyMail.com: ‘Yeah, I did cheat on my wife, yeah… I stood up and took accountability for it and apologized. And that’s [the] end of story.’
Messy: Bullock and the Monster Garage host, 54, met after bringing her motorcycle-obsessed godson a trip to West Coast Choppers’s Long Beach headquarters for Christmas in 2003 (pictured in 2010)
Ryan Gosling (2002-2003)
The two stars met while filming the psychological thriller, Murder by Numbers, in 2001.
Despite their 16-year age gap, their professional relationship eventually turned romantic.
When asked by Cosmopolitan if they were ‘just friends,’ she admitted: ‘If you were to add the word ‘just,’ it would probably be a bit of a lie. So, I’d say we’re friends.’
While speaking about Gosling, the star revealed he taught her how ‘to chill’ and ‘disregard all that isn’t important.’
‘He’s like a little Buddha,’ she said.
Their nearly two-year romance came to an end in 2003, but the duo remained amicable.
In 2011, he blamed ‘show business’ for their split.
‘When both people are in show business, it’s too much show business. It takes all of the light, so nothing else can grow,’ he told The Independent.
He also called her and other ex-girlfriend Rachel McAdams ‘the greatest girlfriends of all time.’
‘I haven’t met anybody who could top them,’ he admitted, months before meeting his wife, Eva Mendes.
Costars-turned-lovers: Bullock and Gosling met while filming the psychological thriller, Murder by Numbers, in 2001
Bob Schneider (1991-2001)
Bullock dated the Texas–based musician from 1999 to 2001.
‘As celebrities go, Bob and I have a very low-key relationship,’ she told Cinema.com in 2000. ‘It’s something I learned through trial and error.’
She admitted: ‘Dating is complicated for me. I have a fear of saying the l-word. Oh my God! I always feel like the minute I say it the sky will fall.’
‘Bob and I talk German all the time to each other, which is terribly funny because I’m so bad at it. Maybe saying ‘I love you’ in German could be easier for me,’ she continued.
His track Blue Skies for Everyone is in her 2000 film Gun Shy and his song, Bullets, is featured on her 2000 action comedy Miss Congeniality soundtrack.
Bullock and Bob Schneider dated from 1999 to 2001 (seen in 2000)
Matthew McConaughey (1996- 1998)
The Virginia native fell head over heels for Matthew McConaughey after meeting him on the set of the 1996 film A Time To Kill.
The former couple managed to quietly date in secret for two years, until parting ways in 1998.
In 2003 when reflecting on remaining good friends over the years, Bullock said: ‘It’s the work we both put in. There’s a great amount of respect and love. I feel very cared for by Matthew. No matter where he is in his life or where I am in mine—he could be married—I know we would stay close.’
While presenting her with the Decade of Hotness award at the 2014 Guys Choice awards, he quipped: ‘I’ve worked with you. I’ve tried to kiss you, successfully and unsuccessfully. I’ve been directed by you, in a short film and also to the exit of many bars.’
Additionally, he has vocalized his desire to work together on another film.
‘[Sandra] and I have another version of our relationship to put on film, and we’re looking for something. She’s not a little girl. She’s a woman. She could run a country,’ he previously told Playboy.
Love on set: The Virginia native fell head over heels for Matthew McConaughey after meeting him on the set of the 1996 film A Time To Kill; seen in 1999
Don Padilla (1996)
The Golden Globe winner and film technician Don Padilla dated for 10 months.
During their short-lived romance, the pair attended the July 1995 premiere of The Net together.
She stated that her then-unidentified boyfriend was a ‘really sweet person.’
Due to his work schedule, she admitted that ‘it’s been rough’ since he works ‘all the time’ and she ‘rarely’ gets to ‘see him.’
‘For a year, I was by myself trying to date and I’m telling you dating was the worst experience I ever had,’ she told Detour, at the time. ‘I seem to have attracted everyone whose intentions were not the best.’
A year later, she reflected on navigating their breakup and her work to Rolling Stone.
‘I had to look at myself and go, ‘I’m responsible for so many things now, what am I choosing to hold close to my heart? And what do I choose to let go of and not control?’ Bullock told the magazine. ‘You learn what you’re made of.’
Less than a year of dating: The Golden Globe winner and film technician Don Padilla dated for 10 months (pictured in 1995)
Troy Aikman (1995)
The All About Steve star and former Dallas Cowboys quarterback Troy Aikman are rumored to have dated briefly in 1995.
While their romance fizzled after just a few dates, the duo reconnected after their respective divorces through a mutual friend during Christmas break in 2013.
He was married to former Cowboys publicist Rhonda Worthey from 2000 to 2011. He went on to remarry Catherine ‘Capa’ Mooty in 2017.
In July 2023, news broke that he and Mooty had officially divorced.
Nothing serious: The All About Steve star and former Dallas Cowboys quarterback Troy Aikman are rumored to have dated briefly in 1995; seen in 2022
Tate Donovan (1990-1995)
America’s sweetheart and the O.C. alum dated for nearly four years, and were even engaged.
After calling off their engagement in 1995, he told Vanity Fair: ‘I can’t explain why things worked out the way they did. We both know why it happened.’
While their romance didn’t work out, it led to her friendship with Jennifer Aniston.
‘We were introduced by our former boyfriend. I say ‘our’ because you and I both partook of this one human being,’ she said during an Interview cover story. ‘We both partook of Tate. … Who was a very patient human being, given that he dated us both.’
Young love: America’s sweetheart and the O.C. alum dated for nearly four years, and were even engaged; seen in 1993
While reflecting on her love life, Bullock told news.com.au that she has ‘never felt like a victim’ and always takes ‘the high road.’
‘The papers said I was ‘unlucky in love.’ And yes, I’ve had a couple of missteps but I also did some things I’m not very proud of to people who were wonderful,’ she admitted.
Over the years, however, she has learned, ‘revenge, anger, resentment only hurts you and it doesn’t make sense because you’re the one falling apart while they don’t even care.’
‘So once you learn forgiveness and to let it go, inevitably you’re shown why that happened and something better steps in every single time,’ she said.
Additionally, she said that ‘marriage isn’t the ultimate ending.’
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